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'''3,4-Methylenedioxy-''N''-hydroxyamphetamine''' ('''MDOH''', '''MDH''', '''N-hydroxytenamphetamine''') is an [[entactogen]], [[psychedelic drug|psychedelic]], and [[stimulant]] of the [[substituted phenethylamine|phenethylamine]] and [[substituted amphetamine|amphetamine]] [[chemical class]]es. It is the ''N''-[[hydroxyl|hydroxy]] [[homology (chemistry)|homologue]] of [[3,4-Methylenedioxyamphetamine|MDA]], and the ''N''-[[desmethyl]] homologue of [[methylenedioxyhydroxymethamphetamine|MDHMA]]. MDOH was first [[Organic synthesis|synthesized]] and [[assay]]ed by [[Alexander Shulgin]].<ref>{{CitePiHKAL}}</ref> In his book ''[[PiHKAL]]'' (''Phenethylamines i Have Known And Loved''), Shulgin listed the dosage range as 100–160&nbsp;mg, and the duration as approximately 3–6 hours.<ref>{{CitePiHKAL}}</ref> He describes MDOH as being very psychedelic and producing increased pleasure in beauty and nature.<ref>{{CitePiHKAL}}</ref> He also mentioned several negative side effects also seen with [[MDMA]] ("Ecstasy") such as difficulty urinating and internal dryness.<ref>{{CitePiHKAL}}</ref>
'''3,4-Methylenedioxy-''N''-hydroxyamphetamine''' ('''MDOH''', '''MDH''', '''N-hydroxytenamphetamine''') is an [[entactogen]], [[psychedelic drug|psychedelic]], and [[stimulant]] of the [[substituted phenethylamine|phenethylamine]] and [[substituted amphetamine|amphetamine]] [[chemical class]]es. It is the ''N''-[[hydroxyl|hydroxy]] [[homology (chemistry)|homologue]] of [[3,4-Methylenedioxyamphetamine|MDA]], and the ''N''-[[desmethyl]] homologue of [[methylenedioxyhydroxymethamphetamine|MDHMA]]. MDOH was first [[Organic synthesis|synthesized]] and [[assay]]ed by [[Alexander Shulgin]].<ref name = "CitePiHKAL">{{CitePiHKAL|name-list-format = vanc }}</ref> In his book ''[[PiHKAL]]'' (''Phenethylamines i Have Known And Loved''), Shulgin listed the dosage range as 100–160&nbsp;mg, and the duration as approximately 3–6 hours.<ref name = "CitePiHKAL" /> He describes MDOH as being very psychedelic and producing increased pleasure in beauty and nature.<ref name = "CitePiHKAL" /> He also mentioned several negative side effects also seen with [[MDMA]] ("Ecstasy") such as difficulty urinating and internal dryness.<ref name = "CitePiHKAL" />


== References ==
== References ==

Revision as of 16:23, 1 January 2020

3,4-Methylenedioxy-N-hydroxyamphetamine
Clinical data
ATC code
  • none
Legal status
Legal status
Identifiers
  • 1-(1,3-Benzodioxol-5-yl)-N-hydroxypropan-2-amine
CAS Number
PubChem CID
ChemSpider
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC10H13NO3
Molar mass195.22 g/mol g·mol−1
3D model (JSmol)
  • CC(CC1=CC2=C(C=C1)OCO2)NO

3,4-Methylenedioxy-N-hydroxyamphetamine (MDOH, MDH, N-hydroxytenamphetamine) is an entactogen, psychedelic, and stimulant of the phenethylamine and amphetamine chemical classes. It is the N-hydroxy homologue of MDA, and the N-desmethyl homologue of MDHMA. MDOH was first synthesized and assayed by Alexander Shulgin.[1] In his book PiHKAL (Phenethylamines i Have Known And Loved), Shulgin listed the dosage range as 100–160 mg, and the duration as approximately 3–6 hours.[1] He describes MDOH as being very psychedelic and producing increased pleasure in beauty and nature.[1] He also mentioned several negative side effects also seen with MDMA ("Ecstasy") such as difficulty urinating and internal dryness.[1]

References

  1. ^ a b c d Shulgin A, Shulgin A (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628.

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